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KR19980016221A - Oxazoline derivatives and process for their preparation - Google Patents

Oxazoline derivatives and process for their preparation Download PDF

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Publication number
KR19980016221A
KR19980016221A KR1019960035755A KR19960035755A KR19980016221A KR 19980016221 A KR19980016221 A KR 19980016221A KR 1019960035755 A KR1019960035755 A KR 1019960035755A KR 19960035755 A KR19960035755 A KR 19960035755A KR 19980016221 A KR19980016221 A KR 19980016221A
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South Korea
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general formula
solvent
hydrogen
compound
alkyl
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KR100189381B1 (en
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김완주
이관순
채기병
김경수
문영호
김남두
이광옥
하태희
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정지석
한미약품 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Epoxy Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

본 발명은 탁솔제조시 중간체로서 유용한 하기 일반식 (Ⅰ)의 신규한 옥사졸린 유도체 및 그의 제조방법에 관한 것이다.The present invention relates to novel oxazoline derivatives of the general formula (I) and useful as intermediates in the preparation of taxanes.

상기식에서, X는 할로겐 원자를 나타내고, Y는 할로겐 또는 수소원자를 나타내며, R은 수소 또는 C1-C3알킬을 나타낸다.In the above formula, X represents a halogen atom, Y represents a halogen or a hydrogen atom, and R represents hydrogen or C 1 -C 3 alkyl.

Description

옥사졸린 유도체 및 그의 제조방법Oxazoline derivatives and process for their preparation

본 발명은 탁솔제조시 중간체로서 유용한 하기 일반식 (Ⅰ)의 신규한 옥사졸린 유도체 및 그의 제조방법에 관한 것이다.The present invention relates to novel oxazoline derivatives of the general formula (I) and useful as intermediates in the preparation of taxanes.

1One 33 22 1One 33 1One 33 22 22 DD 2525 33 1One 33 DD 2525 33 1One 33 DD 2525 33 1One 33 DD 2525 33 1One 33 1One 33 DD 2525 33 1One 33 DD 2525 33 1One 33 1One 33 1One 33 1One 33 1One 33 1One 33 1One 33

Claims (12)

하기 일반식 (Ⅰ)의 옥사졸린 유도체 또는 그의 염:An oxazoline derivative of the general formula (I) or a salt thereof: 상기식에서, X는 할로겐 원자를 나타내고, Y는 할로겐 또는 수소원자를 나타내며, R은 수소 또는 C1-C3알킬을 나타낸다.In the above formula, X represents a halogen atom, Y represents a halogen or a hydrogen atom, and R represents hydrogen or C 1 -C 3 alkyl. 제1항에 있어서, X가 염소이고 Y는 수소 또는 염소인 화합물.2. The compound according to claim 1, wherein X is chlorine and Y is hydrogen or chlorine. 하기 일반식 (Ⅲ)의 화합물을 용매중에서 산촉매 존재하에 하기 일반식 (Ⅳ)의 화합물과 반응시켜 하기 일반식 (Ⅰ)의 화합물을 제조하는 방법:A process for preparing a compound represented by the following general formula (I) by reacting a compound represented by the following general formula (III) with a compound represented by the following general formula (IV) in a solvent in the presence of an acid catalyst: 상기식에서, R, X 및 Y는 제1항에서 정의한 바와 같다.Wherein R, X and Y are as defined in claim 1. 제3항에 있어서, 용매가 테트라하이드로퓨란, 디이소프로필에테르, 메틸 t-부틸에테르, 디옥산, 메탄올, 에탄올, 메틸이소부틸케톤, 아세토니트릴, 에틸아세테이트, 이소프로필아세테이트, n-부틸아세테이트, 디클로로메탄, 클로로포름, 1,2-디클로로에탄, 벤젠, 톨루엔, 크실렌, 디메틸아세트아미드 및 디메틸포름아미드 중에서 선택된 1종 이상인 방법.4. The process of claim 3 wherein the solvent is selected from the group consisting of tetrahydrofuran, diisopropyl ether, methyl t-butyl ether, dioxane, methanol, ethanol, methyl isobutyl ketone, acetonitrile, ethyl acetate, isopropyl acetate, Wherein the solvent is at least one selected from the group consisting of dichloromethane, chloroform, 1,2-dichloroethane, benzene, toluene, xylene, dimethylacetamide and dimethylformamide. 제3항에 있어서, 산촉매가 p-톨루엔설폰산, 메탄설폰산, 트리플루오로메틸설폰산, 피리디늄 p-톨루엔설포네이트 및 엠버라이트 IR-120 중에서 선택된 1종 이상인 방법.The process according to claim 3, wherein the acid catalyst is at least one selected from p-toluenesulfonic acid, methanesulfonic acid, trifluoromethylsulfonic acid, pyridinium p-toluenesulfonate and Amberlite IR-120. 제5항에 있어서, 산촉매가 엠버라이트 IR-120인 방법.6. The method of claim 5, wherein the acid catalyst is Amberlite IR-120. 제3항에 있어서, 반응을 30 내지 100℃의 온도범위에서 수행하는 방법.4. The process according to claim 3, wherein the reaction is carried out at a temperature ranging from 30 to 100 < 0 > C. 제3항에 있어서, 추가로 R이 C1-C3알킬인 일반식 (Ⅰ)의 옥사졸린 화합물을 용매중에서 수용성 염기의 존재하에 가수분해시켜 R이 수소인 일반식 (Ⅰ)의 화합물을 제조하는 방법.4. The method of claim 3, producing a more R compounds of the C 1 -C 3 alkyl in the general formula (Ⅰ) oxazol hydrolyze the sleepy compound in the presence of a water-soluble base in a solvent wherein R is formula (Ⅰ) hydrogen to the How to. 제8항에 있어서, 용매가 유기용매와 물을 부피비로 10:1 내지 100:1로 혼합한 것인 방법.9. The process of claim 8, wherein the solvent is an organic solvent and water in a volume ratio of 10: 1 to 100: 1. 제9항에 있어서, 유기용매가 메탄올, 에탄올, 이소프로필알콜, 테트라하이드로퓨란, 디메틸포름아미드, 디메탈아세트아미드, 아세톤 및 아세토니트릴 중에서 선택된 1종 이상인 방법.10. The method according to claim 9, wherein the organic solvent is at least one selected from the group consisting of methanol, ethanol, isopropyl alcohol, tetrahydrofuran, dimethylformamide, dimethylacetamide, acetone and acetonitrile. 제8항에 있어서, 수용성 염기로 수산화리튬, 수산화나트륨 또는 수산화칼륨을 R이 C1-C3알킬인 일반식 (Ⅰ)의 화합물에 대해 1 내지 2 당량배 사용하는 방법.The method according to claim 8, wherein lithium hydroxide, sodium hydroxide or potassium hydroxide is used as a water-soluble base in an amount of 1 to 2 equivalents based on the compound of the general formula (I) wherein R is C 1 -C 3 alkyl. 제8항에 있어서, 반응을 -20 내지 60℃의 온도범위에서 수행하는 방법.The process according to claim 8, wherein the reaction is carried out at a temperature ranging from -20 to 60 < 0 > C.
KR1019960035755A 1996-08-27 1996-08-27 Oxazoline derivatives and preparation method thereof Expired - Fee Related KR100189381B1 (en)

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KR100189381B1 KR100189381B1 (en) 1999-06-01

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